EP1031593B1 - Composition aqueuse contenant des composés aminofonctionels - Google Patents

Composition aqueuse contenant des composés aminofonctionels Download PDF

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Publication number
EP1031593B1
EP1031593B1 EP00101126A EP00101126A EP1031593B1 EP 1031593 B1 EP1031593 B1 EP 1031593B1 EP 00101126 A EP00101126 A EP 00101126A EP 00101126 A EP00101126 A EP 00101126A EP 1031593 B1 EP1031593 B1 EP 1031593B1
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EP
European Patent Office
Prior art keywords
water
general formula
composition
silicon compounds
content
Prior art date
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Expired - Lifetime
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EP00101126A
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German (de)
English (en)
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EP1031593A3 (fr
EP1031593A2 (fr
Inventor
Burkhard Dr. Standke
Roland Edelmann
Albert-Johannes Dr. Frings
Michael Dr. Horn
Peter Dr. Jenkner
Ralf Dr. Laven
Helmut Dr. Mack
Jaroslaw Dr. Monkiewicz
Günter Switalla
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Evonik Operations GmbH
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Degussa GmbH
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Publication of EP1031593A3 publication Critical patent/EP1031593A3/fr
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/544—Silicon-containing compounds containing nitrogen
    • C08K5/5445—Silicon-containing compounds containing nitrogen containing at least one Si-N bond
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/549—Silicon-containing compounds containing silicon in a ring
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • C09D183/04—Polysiloxanes
    • C09D183/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
    • C23C2222/00—Aspects relating to chemical surface treatment of metallic material by reaction of the surface with a reactive medium
    • C23C2222/20—Use of solutions containing silanes

Definitions

  • the present invention relates to a composition consisting of a Mixture of water-soluble, amino-functional and substantially alkoxy group-free silicon compounds, water, optionally one low content of alcohol and optionally a content of acid consists.
  • such compositions are free of Solvents, with water and alcohols from the amount of solvent with exception of.
  • Aminosilanes are known as water-soluble adhesion promoters. Also are water-based compositions with multifunctional Organopolysiloxanes known as adhesion promoters, cf. EP 0 716 128 A2. at These systems will be the cause of the improvement of the Water solubility essentially the amino-functional groups attributed.
  • a number of other application areas for amino-functional silanes or siloxanes are: The use in coating systems, in the field of corrosion protection, for the biocidal finishing of surfaces, in the treatment of wood, in the production of electrophotographic toner, as an ingredient in aminosilicone fluids (US 5 077 421), as a component in epoxy resins [Chemical Abstracts (1991) - CA 114 : 83579s], for the preparation of organically modified glasses (EP 0 223 987 A2), as anticancer agents [Chemical Abstracts (1983) - CA 99: 133650c], for the modification of glass and glass fiber surfaces, in wastewater treatment, for pigment treatment, as Component in catalysts and for their preparation (US 4 053 534), as flocculants, to name just a few examples.
  • Alkoxysilane oligomers to reduce the agglomeration of inorganic Use powder. It can be seen from US 5,543,173 that such Preparations also contain significant amounts of alcohol and above In addition, said silanol oligomers still significant amounts of hydrolysis alcohol can release.
  • aminosilanes such as. B. aminopropyltriethoxysilane or Aminopropyltrimethoxysilane, water-soluble, they allow a water-based application, eg. B. in aqueous glass fiber sizes. Disadvantageous here, too, is the formation of .alpha. Occurring during the hydrolysis Alcohol.
  • the aminopropyltriethoxysilane develops at aqueous application to approx. 62% of the silane weight of ethanol used Hydrolysis product.
  • Ethanol uses the flammable, water-soluble liquid Flash point of such application solutions down, which in general requires the use of expensive, explosion-proof equipment.
  • Aminoalkoxysilanes can on hydrolysis a maximum of one silane triol group per Forming a molecule.
  • Silanols and other silanol functions can be used with each other or with other OH functions, for example with OH functions from a substrate or from dissolved, emulsified or suspended monomeric or polymeric substances. Such OH functions could z.
  • silane triol units per molecule are desirable.
  • Silanetriol units per molecule are obtained in the hydrolysis of To (trialkoxysilylalkyl) amines. Aqueous solutions of such compounds but they are not stable. They tend to gel and flocculate and are thus not suitable for application.
  • the invention was based on the object, a water-based agent to provide bis (trihydroxysilylalkyl) amines or derived therefrom Contains siloxanes, has the lowest possible content of alcohol, Moreover, it is solvent - free and contains silicon compounds that are used in the are essential alkoxy phenomenonoko.
  • a low-viscosity, generally clear, largely storage-stable composition which consists of a mixture of water-soluble, amino-functional and substantially alkoxy phenomenonabier silicon compounds, water, optionally a low content of alcohol and optionally a content of acid is available, by at least one aminosilane of the general formula III NH 2 [(CH 2 ) 2 NH] x (CH 2 ) 3 Si (OR) 3 wherein x is 0, 1 or 2 and R is a linear or branched alkyl group having 1 to 4 C atoms, and / or its Ankondensations occur and at least one aminosilane of general formula IV (RO) 3 Si (CH 2 ) 3 [NH (CH 2 ) 2 ] y NH [(CH 2 ) 2 NH] z (CH 2 ) 3 Si (OR) 3 wherein y and z are 0, 1 or 2 and the same or different and R is a linear or branched alkyl group having 1 to 4 C atoms
  • the present composition is commonly used in is obtained in a liquid, well applied form and is usually also in the essentially free of solvents.
  • Silicon compounds of general formulas I and II are higher Crosslinking density in the polymeric cured siloxane structure and a significant improvement of mechanical, chemical and thermal Properties of Treated Substances, e.g. Composite materials, such. B. glass fiber and mineral fiber reinforced plastics, paints and varnishes, filled Polymers are achieved.
  • the composition of the invention may also be used in diluted with water at any ratio, with no additional Hydrolysealcohol arises.
  • the present composition excellent storage stability for more than 12 months.
  • the present invention thus relates to a composition which consists of a mixture of water-soluble, amino-functional and substantially alkoxy phenomenonabier silicon compounds, water, optionally a content of alcohol and optionally a content of acid wherein the composition is silicon compounds of the general formula I.
  • the composition according to the invention has a content to alcohol of less than 5 wt .-%, particularly preferably less as 1% by weight, most preferably from 1 ppm by weight to 0.5 wt .-%, on.
  • a composition Methanol and / or ethanol as alcohol included.
  • a composition according to the invention has a content Silicon compounds of less than 60 wt .-%, preferably less as 50 wt .-%, particularly preferably the content is Silicon compounds at 0.01 to 40 wt .-%, and most preferably it is 0.5 to 40 wt .-%.
  • a composition of the invention the weight ratio of the silicon compounds of general formula I. and the general formula II in I / II ⁇ 1, wherein the general formulas I and II, which is generally understood to be in equilibrium silanols and siloxanes present.
  • the pH of a composition of the invention may be in the range between 1 to 14 lie. Suitably it is at a value ⁇ 11, preferably in the range of 4 to 9.
  • the present invention further provides the process for the preparation of a composition which consists of a mixture of water-soluble, amino-functional and substantially alkoxy phenomenonabier silicon compounds, water, optionally a content of alcohol and optionally a content of acid, which is characterized in that at least one Aminosilane of the general formula III NH 2 [(CH 2 ) 2 NH] x (CH 2 ) 3 Si (OR) 3 wherein x is 0, 1 or 2 and R is a linear or branched alkyl group having 1 to 4 C atoms, and / or its Ankondensations occur and at least one aminosilane of general formula IV (RO) 3 Si (CH 2 ) 3 [NH (CH 2 ) 2 ] y NH [(CH 2 ) 2 NH] z (CH 2 ) 3 Si (OR) 3 wherein y and z are 0, 1 or 2 and the same or different and R is a linear or branched alkyl group having 1 to 4 C atoms, and / or its Ankonden
  • aminosilanes of the general formula III H 2 N (CH 2 ) 3 Si (OCH 3 ) 3 (AMMO), H 2 N (CH 2 ) 3 Si (OC 2 H 5 ) 3 (AMEO), H 2 N (CH 2 ) 2 NH (CH 2 ) 3 Si (OCH 3 ) 3 (DAMO), H 2 N (CH 2 ) 2 NH (CH 2 ) 2 NH (CH 2 ) 3 Si (OCH 3 ) 3 (TRIAMO), and as compounds according to formula IV preferably (H 3 CO) 3 Si (CH 2 ) 3 NH (CH 2 ) 3 Si (OCH 3 ) 3 (Bis-AMMO), (H 5 C 2 O) 3 Si (CH 2 ) 3 NH (CH 2 ) 3 Si (OC 2 H 5 ) 3 (bis-AMEO), (H 3 CO) 3 Si (CH 2 ) 3 NH (CH 2 ) 2 NH (CH 2 ) 3 Si (OC 2 ) 3 Si (OC 3 Si (OC 3 Si (OC 3 Si (OC
  • the process according to the invention is carried out in such a way that aminosilanes of the general formulas III and IV are mixed together hydrolyzed and the resulting hydrolysis alcohols removed by distillation Das Mixing of the alkoxysilanes can occur in a temperature range between solid and Boiling point of the silanes used.
  • the concentration of silanes in the aqueous Solution to a value ⁇ 60 wt .-%, preferably ⁇ 50 wt .-%, especially preferably 0.01 to 40% by weight and most preferably 0.5 to 40% by weight.
  • a deviation from these parameters can lead to gelation or a strong cloudiness.
  • Alcohol is formed in the hydrolysis of alkoxysilanes.
  • the hydrolysis can be carried out at a temperature in the range of 0 to 100 ° C.
  • the hydrolysis is carried out at a Temperature ⁇ 100 ° C, particularly preferably at ⁇ 90 ° C and completely especially preferably at ⁇ 60 ° C.
  • the hydrolysis is carried out in the process according to the invention at a pH in the range of 4 to 12.
  • silane mixture or system Silangemisch / water or the already hydrolyzed system an acid or base to adjust the Add pH.
  • At least one is added Brönstedt acid too.
  • you can also use a Brönstedt base For example, potassium hydroxide solution, caustic soda and ammonia or Amines, just to name a few.
  • Particularly preferred acids are hydrogen chloride, sulfuric acid, Nitric acid, perchloric acid, formic acid, acetic acid and / or Propionic acid.
  • the concentration is lowered in the method according to the invention Hydrolysealkohol by distillation, wherein the distillation is preferably at a temperature ⁇ 90 ° C, more preferably at ⁇ 60 ° C, and suitably carried out under reduced pressure.
  • the distillation can advantageously be carried out via a distillation column and continue until the top of the column no alcohol can be determined, wherein the desired product results in the swamp and if necessary, be further worked up. If turbidities occur should be able to do this by filtration, sedimentation, centrifugation or similar standard procedures are removed from the product.
  • the application of the composition according to the invention can be made concentrated solution or diluted with water solution. at Dilution with water can increase the storage stability of the so diluted Composition can be improved by adding acid.
  • the pH of the diluted composition is adjusted to a value ⁇ 9.
  • the products obtained according to the invention have the particular advantage that they are water-soluble, spontaneously in any proportion with water mix, a high content of bis (trihydroxysilylalkyl) amine and whose derived siloxanes contain and are substantially alcohol-free.
  • compositions of the invention find excellent results Use as a water-soluble primer, as an ingredient in Coating systems and in anti-corrosion agents, especially in the coating of metal, for the biocidal finishing of surfaces, for the treatment of wood, for electrophotographic toners, as an ingredient in aminosilicone fluids, as an ingredient in epoxy resins, phenolic resins, unsaturated polyester resins (UP resins), acrylic resins, as an ingredient in organically modified glasses, for pharmaceutical and cosmetic Products for the modification of glass and mineral surfaces as well as glass and glass Mineral fiber surfaces, including glass beads, glass fabrics, Architectural fabrics, just to name a few, for the Wastewater treatment, for pigment treatment, as an ingredient in the Preparation of catalysts, as flocculants, as an ingredient in paints and paints, in the manufacture of artificial stones, to increase strength of flat glass, hollow glass and laminated glass as well as adhesion promoter for UV-curing Polymers, in particular acrylic compounds on glass and other substrates.
  • UP resins unsaturated polyester resins
  • acrylic resins as
  • 120g high boilers are mixed with 480g AMEO 1 250,0 g water are presented in the stirred reactor.
  • the aminosilane mixture is within of 30 to 40 minutes added via the metering device.
  • the rising Temperature from room temperature to about 50 ° C on.
  • the approach will be 3 hours stirred at 50 ° C.
  • about 450g ethanol / water mixture distilled off (T: 39 to 41 ° C, p: 130 to 100 mbar, about 70 wt .-% ethanol, ca. 30% by weight of water).
  • the final product will end up with water on Weight of 1 500 g set (40 wt .-% "silanes" in water).
  • the turbidity of the product can be controlled by a conventional filter be improved.
  • the filter residue is less than 0.2 wt .-% of Total amount of product.
  • the final product is stable for more than 12 months.
  • 120 g high boilers are mixed with 480 g AMEO. 1 050 g of water submitted in a stirred reactor.
  • the aminosilane mixture becomes within 30 to 40 minutes added via the metering device.
  • the approach becomes Stirred for 3 hours at 50 ° C.
  • about 450 g of ethanol / water mixture distilled off (T: 39 to 41 ° C, p: 130 to 100 mbar, about 70 wt .-% Ethanol, about 30% by weight of water).
  • the final product will end up with water adjusted to a weight of 1 200 g (50 wt .-% "silanes" in water).
  • the turbidity of the product can be controlled by a conventional filter be improved.
  • the filter residue is less than 0.5 wt .-% of Total amount of product. After filtration, the turbidity is ⁇ 10 TE / F (DIN / EN 27 027).
  • 120 g high boilers are mixed with 180 g AMEO. 2 000 g of water submitted in a stirred reactor.
  • the aminosilane mixture becomes within 30 to 40 minutes added via the metering device and then with Formic acid adjusted to a pH of 6.
  • the approach will be 3 hours stirred at 50 ° C.
  • about 500 g of ethanol / water mixture distilled off T: 39 to 41 ° C, p: 130 to 100 mbar).
  • the final product will be on Adjusted to a weight of 3,000 g with water (10% by weight of "silanes”) in water).
  • the turbidity of the product may be via an ordinary filter chute be improved.
  • the filter residue is less than 0.5 wt .-% of Total amount of product. After filtration, the turbidity is ⁇ 10 TE / F (DIN / EN 27 027).
  • the turbidity of the product may be via an ordinary filter chute be improved.
  • the filter residue is less than 0.5 wt .-% of Total amount of product. After filtration, the turbidity is ⁇ 10 TE / F (DIN / EN 27 027).
  • 120g high boilers are mixed with 480g TRIAMO.
  • 1 110g of water are presented in the stirred reactor.
  • the aminosilane mixture is within from 30 to 40 minutes added via the metering device and then adjusted to pH 6 with formic acid (240 g).
  • the temperature rises from room temperature to approx. 50 ° C.
  • Of the Batch is stirred for 3 hours at 50 ° C.
  • T 39 to 41 ° C, p: 130 to 100 mbar
  • the final product is finished with water to a weight of 1 500 g adjusted (40 wt .-% "silanes" in water).
  • the turbidity of the product may be via an ordinary filter chute be improved.
  • the filter residue is less than 0.5 wt .-% of Total amount of product. After filtration, the turbidity is ⁇ 10 TE / F (DIN / EN 27 027).

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Paints Or Removers (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Silicon Polymers (AREA)

Claims (15)

  1. Composition qui consiste en un mélange de composés du silicium, fonctionnalisés par un groupe amino, pour l'essentiel dépourvus de groupe alkoxy, et solubles dans l'eau,, éventuellement avec une teneur en alcool et éventuellement une teneur en acide, et qui renferme des composés du silicium de formule générale I : NH2[CH2)2NH]x(CH2)3SiO1.5 dans laquelle x est égale à 0, 1 ou 2, et de formule générale II : (SiO1,5)(CH2)3 [NH(CH2)2]y NH [(CH2)2NH]z (CH2)3SiO1.5 dans laquelle y et z sont égaux à 0, 1 ou 2 et sont identiques ou différents.
  2. Composition selon la revendication 1,
    caractérisée par
    une concentration en alcool Inférieure à 5 % en poids.
  3. Composition selon la revendication 1 ou 2,
    caractérisée par
    une valeur de pH Inférieure à 11.
  4. Composition selon l'une des revendications 1 à 3,
    caractérisée par
    une concentration en composés du silicium de moins de 60 % en poids.
  5. Composition selon l'une des revendications 1 à 4,
    caractérisée en ce que
    le rapport en poids des composés du silicium de formule générale I et de formule générale II est I : II ≥ 1.
  6. Composition selon l'une des revendications 1 à 5,
    caractérisée par
    des composés du silicium conformément aux formules I et II y compris les sllanols et les siloxanes qui se trouvent pour cela respectivement, en équilibre.
  7. Procédé de préparation d'une composition qui consiste en un mélange à base de composés du silicium, fonctionnalisés par un amino. essentiellement dépourvus de groupes alkoxy, et solubles dans l'eau, éventuellement avec une teneur en alcool et éventuellement une teneur en acide,
    caractérisé en ce qu'
    on mélange au moins un aminosilane de formule générale III : NH2[(CH2)2NH]x(CH2)3Si(OR)3 dans laquelle x est égale à 0, 1 ou 2 et R représente un groupe alkyle linéaire ou ramifié ayant de 1 à 4 atomes de carbone, et/ou leurs produits de condensation et au moins un aminosilane de formule générale IV : (RO)3Si(CH2)3[NH(CH2)2]yNH[(CH2)2NH]z(CH2)3Si(OR)3 dans laquelle y et z sont égaux à 0, 1 ou 2 et sont identiques ou différents
    et/ou leurs produits de condensation,
    on ajoute de l'eau et éventuellement un acide, on hydrolyse et on élimine l'alcool d'hydrolyse pour l'essentiel.
  8. Procédé selon la revendication 7,
    caractérisé en ce qu'
    on met en oeuvre les aminosilanes de formule générale III et de formule générale IV dans un rapport pondéral III/IV ≥ 1.
  9. Procédé selon la revendication 7 ou la revendication 8,
    caractérisé en ce qu'
    on exécute l'hydrolyse à une température Inférieure à 100°C.
  10. Procédé selon l'une des revendications 7 à 9,
    caractérisé en ce qu'
    on exécute l'hydrolyse à une valeur de pH allant de 4 à 12.
  11. Procédé selon l'une des revendications 7 à 10,
    caractérisé en ce qu'
    on ajoute comme acide au moins un acide de Brönstedt.
  12. Procédé selon l'une des revendications 7 à 11,
    caractérisé en ce qu'
    on abaisse la concentration en alcool d'hydrolyse par distillation.
  13. Procédé selon l'une des revendications 7 à 12,
    caractérisé en ce qu'
    on ajuste la valeur de pH de la composition à une valeur < 11.
  14. Composition accessible selon l'une des revendications 7 à 13.
  15. Utilisation d'une composition selon les revendications 1 à 14 comme adjuvant d'adhésion soluble dans l'eau, comme constituant dans des systèmes de revêtement, ainsi que dans des agents protecteurs contre la corrosion, pour l'équipement blocide des surfaces, pour le traitement du bois, comme toner électro photographique, comme constituant dans des liquides d'aminosilicone, comme constituant dans des résines époxyde, phénol, UP ou acryliques, comme constituants dans des verres modifiés organiquement pour la production de produits pharmaceutiques et cosmétiques, pour la modification de surfaces de verre et de minéraux, ainsi que de la surface de fibres de verre et de minéraux, pour la production de pierres artificielles, pour le traitement des eaux usées, pour la modification des surfaces et le traitement de pigments pour la production de catalyseurs, comme agent de floculation, comme constituant dans des colorants et des laques, pour l'augmentation de la solidité du verre plat, du verre creux et composite, ainsi que comme adjuvant d'adhésion pour des polymères réticulant à la lumière UV.
EP00101126A 1999-02-27 2000-01-21 Composition aqueuse contenant des composés aminofonctionels Expired - Lifetime EP1031593B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19908636A DE19908636A1 (de) 1999-02-27 1999-02-27 Wasserbasierende Zusammensetzung aminofunktioneller Siliciumverbindungen
DE19908636 1999-02-27

Publications (3)

Publication Number Publication Date
EP1031593A2 EP1031593A2 (fr) 2000-08-30
EP1031593A3 EP1031593A3 (fr) 2001-09-05
EP1031593B1 true EP1031593B1 (fr) 2003-10-29

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US (1) US6534667B1 (fr)
EP (1) EP1031593B1 (fr)
JP (1) JP4707791B2 (fr)
DE (2) DE19908636A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102007058712A1 (de) 2007-12-06 2009-06-10 Evonik Degussa Gmbh Modulares Sol-Gel-System und Verfahren zum Einstellen der Eigenschaften des Sol-Gel-Systems
US8298679B2 (en) 2007-08-28 2012-10-30 Evonik Degussa Gmbh Aqueous silane systems based on bis(trialkoxysilylalkyl)amines
US8673999B2 (en) 2010-03-08 2014-03-18 Dow Global Technologies Llc Water based primer composition for isocyante and silane functional adhesives
EP3611236A1 (fr) 2018-08-17 2020-02-19 Evonik Operations GmbH Composition stable au stockage, aqueuse, contenant du n-(2-aminoéthyl)-3-aminopropylsiloxane chlorhydrates substitués par n-benzyle, leur procédé de production et d'utilisation

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US6541671B1 (en) 2002-02-13 2003-04-01 The Regents Of The University Of California Synthesis of 2H- and 13C-substituted dithanes
DE19961972A1 (de) 1999-12-22 2001-06-28 Degussa Organosilan- und/oder Organosiloxan-haltige Mittel für gefülltes Polyamid
US6416817B1 (en) * 2000-03-03 2002-07-09 Dow Corning Sa Barrier coatings having bis-silanes
EP1195417B1 (fr) 2000-10-05 2009-10-14 Evonik Degussa GmbH Nanocapsules organosiliciés
EP1195416A3 (fr) * 2000-10-05 2005-12-28 Degussa AG Nanocapsules organosiliciés polymérisables
DE10056344A1 (de) 2000-11-14 2002-05-16 Degussa n-Propylethoxysiloxane, Verfahren zu deren Herstellung und deren Verwendung
DE10056343A1 (de) 2000-11-14 2002-05-16 Degussa Kontinuierliches Verfahren zur Herstellung von Organoalkoxysiloxanen
DE10100384A1 (de) * 2001-01-05 2002-07-11 Degussa Verfahren zur Modifizierung der Funktionalität von organofunktionellen Substratoberflächen
EP1249470A3 (fr) 2001-03-30 2005-12-28 Degussa AG Composition fortement chargée en nano et/ou microcapsules hybrides à base de silice organique pâteuse pour des revêtements résistants aux rayures et à l'abrasion
EP1245627B1 (fr) 2001-03-30 2007-07-04 Degussa GmbH Compositions pour revêtements résistantes aux rayures et à l'abrasion contenant des systèmes nano-microhybrides ou microhybrides à base de composés organiques de silice
DE10141687A1 (de) 2001-08-25 2003-03-06 Degussa Siliciumverbindungen enthaltendes Mittel zur Beschichtung von Oberflächen
DE10151264A1 (de) 2001-10-17 2003-04-30 Degussa Aminoalkylalkoxysiloxanhaltige Gemische, deren Herstellung und deren Verwendung
DE10153803A1 (de) 2001-11-05 2003-05-15 Degussa Korrosionsinhibitor für Stahlbeton
EP1331238A3 (fr) * 2002-01-23 2004-01-14 Degussa AG Mélange d'oligomères de polysiloxanes linéaires et cycliques, leur préparation et leur application
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EP1031593A2 (fr) 2000-08-30
JP4707791B2 (ja) 2011-06-22
US6534667B1 (en) 2003-03-18

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